1,2-Dimethoxyethane → 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

関与物質

役割	名称	HCID	仕込み量
反応物	1,2-Dimethoxyethane	HCID 8071	—
反応物	Sodium Carbonate	HCID 10340	—
反応物	2-Fluorophenylboronic acid	HCID 2734354	—
反応物	6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline	HCID 54775608	—
触媒	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
溶媒	Dichloromethane	HCID 6344	—
生成物	6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline	HCID 59341829	74.5%

反応条件

温度	80 °C

反応手順

A mixture of DME (3.0 mL) and 1 M aqueous Na2CO3 (0.88 mL) was degassed by bubbling in Argon for 10 minutes. The mixture was transferred via syringe to a vial containing 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.29 mmol), 2-fluorophenylboronic acid (45 mg, 0.32 mmol) and Pd(dppf)2Cl2.CH2Cl2 (6.2 mg, 0.01 mmol). The vial was capped and heated to 80° C. for 3.5 hours. The crude reaction mixture was diluted with dichloromethane then washed with water. The dichloromethane was dried over Na2SO4, filtered and concentrated by rotary evaporation. The residue was purified by column chromatography using gradient elution with ethyl acetate and dichloromethane to afford 6-((6-(2-fluorophenyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (77 mg, 74%).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US07732604B2
出典データセット	uspto-grants-2010_06
ORD ID	ord-809f753e12c145829877418314079bb0
出典メモ	uspto-grants-2010_06